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Enzymatic Synthesis of Epoxidized Metabolites of Docosahexaenoic, Eicosapentaenoic, and Arachidonic Acids
Published on: June 28, 2019
Epoxidación enzimática secuencial involucrada en la biosíntesis del poliéter lasalocida
Atsushi Minami1, Mayu Shimaya, Gaku Suzuki
1Division of Chemistry, Graduate School of Science, Hokkaido University, Sapporo 060-0810, Japan.
Journal of the American Chemical Society
|April 18, 2012
Resumen
Las monooxigenasas que contienen flavina (FMOs) catalizan la epoxidación enantioselectiva, un paso clave en la construcción de esqueletos de poliéteres como el lasalocid. Este estudio aclara el mecanismo enzimático de la biosíntesis de poliéteres.
Área de la Ciencia:
- La bioquímica es la bioquímica.
- Química orgánica es la química orgánica.
- Biología Molecular Biología Molecular
Sus antecedentes:
- Los esqueletos de poliéteres son cruciales en productos naturales como los poliéteres ionóforos.
- La epoxidación enantioselectiva y la apertura de epóxido regioselectivo son pasos sintéticos clave.
- Las monooxigenasas que contienen flavina (FMOs) son enzimas potenciales para la oxidación en la biosíntesis de poliéteres.
Objetivo del estudio:
- Para investigar el papel de Lsd18, un FMO, en la biosíntesis del poliéter lasalocida.
- Comprender el mecanismo enzimático de la epoxidación enantioselectiva en la construcción de poliéteres.
Principales métodos:
- Análisis in vivo e in vitro de la enzima Lsd18.
- El uso de imitaciones de sustratos, incluidas las olefinas simples y los dienes truncados.
- Caracterización de los productos de la epoxidación.
Principales resultados:
- Lsd18 realiza la epoxidación enantioselectiva de una manera gradual.
- La enzima produce mono- o bis-epoxidos de tipo natural.
- Demostró la participación de los FMO en la biosíntesis del poliéter de lasalocida.
Conclusiones:
- Lsd18, una monooxigenasa que contiene flavina, es crucial para la biosíntesis del lasalocida.
- El estudio aclara la vía enzimática para la construcción de esqueletos de poliéter.
- Proporciona información sobre el mecanismo de epoxidación enantioselectiva por etapas.
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